US3176008A - 5-phenyl-benzotriazepin-2-one compounds and their production - Google Patents
5-phenyl-benzotriazepin-2-one compounds and their production Download PDFInfo
- Publication number
- US3176008A US3176008A US222940A US22294062A US3176008A US 3176008 A US3176008 A US 3176008A US 222940 A US222940 A US 222940A US 22294062 A US22294062 A US 22294062A US 3176008 A US3176008 A US 3176008A
- Authority
- US
- United States
- Prior art keywords
- benzotriazepin
- phenyl
- compounds
- dihydro
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- LLPGEPRZHOMDHC-SSZFMOIBSA-N 2-[(z)-c-phenylcarbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(N)C=1C(=N/N)\C1=CC=CC=C1 LLPGEPRZHOMDHC-SSZFMOIBSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- -1 phenyl 2H 1, 3,4-benzotriazepin-2-one Chemical compound 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- KJCLYACXIWMFCC-UHFFFAOYSA-M sodium;5-benzoyl-4-hydroxy-2-methoxybenzenesulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 KJCLYACXIWMFCC-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
- C07D255/04—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 condensed with carbocyclic rings or ring systems
Definitions
- This invention relates to a new class of psychotherapeutic heterocyclic compounds having valuable properties as anticonvulsants. These compounds are substituted 1,3-dihydro--aryl-2H-l,3,4benzotriazepin 2 ones and have the general formula:
- a tertiary amine is employed together with a suitable inert solvent in order to react with the hydrogen chloride liberated in the reaction.
- suitable tertiary amines include trirnethylamine, triethylamine, tributylamine and dimethylaniline.
- Suitable inert solvents include chloroform, methylene chloride, benzene and toluene.
- Method I it is recommended to slowly add a solution of phosgcne to a cooled solution containing the hydrazone and the tertiary amine.
- the reaction temperature during this addition should not exceed about 10 C.
- the mixture is stirred at room temperature, filtered and the filtrate is evaporated to dryice ness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal and the product precipitates on standing.
- the benzophenone and the hydrazino acid ester reactant are heated under autogenous pressure at a temperature ranging from about to about 225 and preferably at C.
- the mixture is then cooled to room temperature, diluted with ethanol and filtered.
- the product precipitates upon standing.
- Example 1 A solution of 12 g. of 12.5% phosgene in benzene solution is added dropwise to a cooled solution of 3.2 g. of Z-amino-benzophenone hydrazone and 5 ml. of triethylamine in 50 ml. of benzene. After addition is completed the mixture is stirred at room temperature for one hour, filtered, and the filtrate evaporated to dryness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal. On standing 1,3-dihydro-5- phenyl-ZI-l-l,3,4-benzotriazepin-2-one, M.P. 238-2395 C., precipitates. Analysis calcd. for C I-1 N 02 C, 70.87; H, 4.68; N, 17.70. Found: C, 70.69; H, 4.53; N, 18.04.
- Example 2 A solution of 8 g. of 12.5% phosgene in benzene solution is added dropwise to a cooled solution of 2 g. of 2-amino-S-methylbenzophenone hydrazone and 3 ml. of triethylamine in 50 ml. of benzene. The mixture is stirred an additional hour at room temperature, filtered, and the filtrate evaporated to dryness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal. On standing 7-methyl-1,3-dihydro-5-phenyl-2H l,3,4-benzotriazepin-2-one, M.P. 253254.5 C., is obtained. Analysis calcd. for C H N O: C, 71.70; H, 5.21; N, 16.72. Found: C, 71.61; H, 5.43; N, 16.64.
- Example 3 A mixture of 5 g. of 2-amino-S-chlorobenzophenone and 5 ml. of ethyl hydrazine carboxylate is heated at 190 for one hour. The mixture is cooled, diluted with 75 ml. of ethanol and filtered. On standing 7-chloro-1,3-dihydro-5-phenyl-2H-l,3,4-benzotriazepin-2-one, MI. 246- 248 C., precipitates. Analysis calcd. for C l-i N OClz C, 61.89; H, 3.72; N, 15.47. Found: C, 61.65; H, 3.95; N, 15.09.
- Example 4 7-trifluoromethyl 1,3 dihydro 5 phenyl 2H 1, 3,4-benzotriazepin-2-one is prepared by heating 5 g. of 2-aminoS-trifluoromethyl benzophenone with 5 ml. of ethyl hydrazine carboxylate as described in Example 3.
- Example 5 7-bromo 1,3 dihydro 5 phenyl-2H-1,3,4-benzotriazepin-Z-one is prepared by heating 5 g. of Z-arnino-S- bromo benzophenone with 5 ml. ethyl hydrazine carboxylate, as described in Example 3.
- Example 6 As described in Example 3, 7-chloro-1,3-dihydro-5-ochlorophenyl-ZH-l,3,4-benzotriazepin-2-one is prepared by heating 5 g. of 2-amino-2'-5-dichloro benzophenone with ethyl hydrazine carboxylate.
- Example 7 As described in Example 3, 7-nitro-1,3-dihydro-5- phenyl-2H-l,3,4-benzotriazepin-2-one is prepared by heating 5 g. of Z-amino-S-nitro benzophenone with 5 ml. of ethyl hydrazine carboxylate.
- the compounds of this invention may be combined with suitable diluents, solvents, carriers and excipients, as required to provide dosage forms suitable for oral or parenteral administration.
- N ⁇ C N/ I 7 Ar wherein X and Ar are as hereinabove.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
United States Patent 3,176,008 S-PI-[ENYL-BENZGTRIAZEPIN-Z-0NE CUM- POUNDS AND THEIR PRGDUCTION Theodore S. Sulkowski, Narherth, and Scott J. Childress,
Newtown Square, Pa., assignors to American Home Products Corporation, New Yorlr, N.Y., a corporation of Delaware No Drawing. Filed Sept. 11, 1962, Ser. No. 222,940 7 Claims. (Cl. 260239.3)
This invention relates to a new class of psychotherapeutic heterocyclic compounds having valuable properties as anticonvulsants. These compounds are substituted 1,3-dihydro--aryl-2H-l,3,4benzotriazepin 2 ones and have the general formula:
NH \c I Ar I METHOD I h NH:
c=o X X i C NH COG] I N 1 'i' 2 \czN/ Ar l II I An alternative method for preparing the present compounds consists in heating a Z-amino-benzophenone (III) with a hydrazine acid ester as shown in the following equation:
where Y is an alkoxy group.
In preparative Method 1, a tertiary amine is employed together with a suitable inert solvent in order to react with the hydrogen chloride liberated in the reaction. Suitable tertiary amines include trirnethylamine, triethylamine, tributylamine and dimethylaniline. Suitable inert solvents include chloroform, methylene chloride, benzene and toluene.
For best results in carrying out Method I, it is recommended to slowly add a solution of phosgcne to a cooled solution containing the hydrazone and the tertiary amine. Preferably, the reaction temperature during this addition should not exceed about 10 C. After the addition of phosgene is completed, the mixture is stirred at room temperature, filtered and the filtrate is evaporated to dryice ness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal and the product precipitates on standing.
In Method II, the benzophenone and the hydrazino acid ester reactant are heated under autogenous pressure at a temperature ranging from about to about 225 and preferably at C. The mixture is then cooled to room temperature, diluted with ethanol and filtered. The product precipitates upon standing.
The following Examples illustrate the practice of this invention:
Example 1 A solution of 12 g. of 12.5% phosgene in benzene solution is added dropwise to a cooled solution of 3.2 g. of Z-amino-benzophenone hydrazone and 5 ml. of triethylamine in 50 ml. of benzene. After addition is completed the mixture is stirred at room temperature for one hour, filtered, and the filtrate evaporated to dryness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal. On standing 1,3-dihydro-5- phenyl-ZI-l-l,3,4-benzotriazepin-2-one, M.P. 238-2395 C., precipitates. Analysis calcd. for C I-1 N 02 C, 70.87; H, 4.68; N, 17.70. Found: C, 70.69; H, 4.53; N, 18.04.
Example 2 A solution of 8 g. of 12.5% phosgene in benzene solution is added dropwise to a cooled solution of 2 g. of 2-amino-S-methylbenzophenone hydrazone and 3 ml. of triethylamine in 50 ml. of benzene. The mixture is stirred an additional hour at room temperature, filtered, and the filtrate evaporated to dryness in vacuo. The residue is dissolved in hot ethanol and treated with charcoal. On standing 7-methyl-1,3-dihydro-5-phenyl-2H l,3,4-benzotriazepin-2-one, M.P. 253254.5 C., is obtained. Analysis calcd. for C H N O: C, 71.70; H, 5.21; N, 16.72. Found: C, 71.61; H, 5.43; N, 16.64.
Example 3 A mixture of 5 g. of 2-amino-S-chlorobenzophenone and 5 ml. of ethyl hydrazine carboxylate is heated at 190 for one hour. The mixture is cooled, diluted with 75 ml. of ethanol and filtered. On standing 7-chloro-1,3-dihydro-5-phenyl-2H-l,3,4-benzotriazepin-2-one, MI. 246- 248 C., precipitates. Analysis calcd. for C l-i N OClz C, 61.89; H, 3.72; N, 15.47. Found: C, 61.65; H, 3.95; N, 15.09.
Example 4 7-trifluoromethyl 1,3 dihydro 5 phenyl 2H 1, 3,4-benzotriazepin-2-one is prepared by heating 5 g. of 2-aminoS-trifluoromethyl benzophenone with 5 ml. of ethyl hydrazine carboxylate as described in Example 3.
Example 5 7-bromo 1,3 dihydro 5 phenyl-2H-1,3,4-benzotriazepin-Z-one is prepared by heating 5 g. of Z-arnino-S- bromo benzophenone with 5 ml. ethyl hydrazine carboxylate, as described in Example 3.
Example 6 As described in Example 3, 7-chloro-1,3-dihydro-5-ochlorophenyl-ZH-l,3,4-benzotriazepin-2-one is prepared by heating 5 g. of 2-amino-2'-5-dichloro benzophenone with ethyl hydrazine carboxylate.
Example 7 As described in Example 3, 7-nitro-1,3-dihydro-5- phenyl-2H-l,3,4-benzotriazepin-2-one is prepared by heating 5 g. of Z-amino-S-nitro benzophenone with 5 ml. of ethyl hydrazine carboxylate.
The compounds of this invention may be combined with suitable diluents, solvents, carriers and excipients, as required to provide dosage forms suitable for oral or parenteral administration.
From the teachings of the foregoing examples, it will be obvious to those skilled in the art how to prepare other similar compounds encompassed within the scope of the broader claims.
What is claimed is:
1. A compound having the formula it \C=O X I N-H o=o 5. 7 methyl 1,3 dihydro 5 phenyl 2H 1,3,4- 7
benzotriazepin-Z-one.
6. 7 chloro 1,3 dihydro S phenyl 2H 1,3,4- benzotriazepin-Z-one.
7. The method which comprises heating together a 2- aminobenzophenone having the formula wherein X is selected from the group consisting of hydrogen, nitro, halogen, lower alkyl and trifluoromethyl and Ar is selected from the group consisting of phenyl and monohalophenyl with a hydrazinoacyl compound having the formula:
wherein Y is a lower alkoxy group, to form a compound having the formula:
N \C=N/ I 7 Ar wherein X and Ar are as hereinabove.
References Cited by the Examiner Busch: Ber. Deut. Chern., vol. 27, pages 28972904 IRVING MARCUS, Primary Examiner.
NICHOLAS S. RIZZO, WALTER A. MODANCE,
Examiners,
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No, 3,176,008
March 30, 1965 Theodore S. Sulkowski et a1.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 3, lines 12 to 18 the formula should appear as shown below instead of as in the patent:
X N H Ar Signed and sealed this 28th day of September 1965.
(SEAL) Allest:
ERNEST W. SWIDER EDWARD J. BRENNER Attesting Officer Commissioner of Patents
Claims (2)
1. A COMPOUND HAVING THE FORMULA
7. THE METHOD WHICH COMPRISES HEATING TOGETHER A 2AMINOBENZOPHENONE HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US222940A US3176008A (en) | 1962-09-11 | 1962-09-11 | 5-phenyl-benzotriazepin-2-one compounds and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US222940A US3176008A (en) | 1962-09-11 | 1962-09-11 | 5-phenyl-benzotriazepin-2-one compounds and their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3176008A true US3176008A (en) | 1965-03-30 |
Family
ID=22834354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US222940A Expired - Lifetime US3176008A (en) | 1962-09-11 | 1962-09-11 | 5-phenyl-benzotriazepin-2-one compounds and their production |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3176008A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094871A (en) * | 1977-02-16 | 1978-06-13 | The Dow Chemical Company | 1,3,4-Benzotriazepine-2-thiones |
| US4144233A (en) * | 1977-02-16 | 1979-03-13 | The Dow Chemical Company | Method for preparing benzo-(1,3,4)-benzotriazepines |
| US4168310A (en) * | 1977-02-16 | 1979-09-18 | The Dow Chemical Company | Psychoactive 1,3,4-benzotriazepine-2-thiones and a method for treating central nervous system depression and anxiety |
| EP0102580A1 (en) * | 1982-08-26 | 1984-03-14 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 1,3,4-benzotriazepines, a method of preparing the same and theire use as medicaments |
| US20060003993A1 (en) * | 2001-11-13 | 2006-01-05 | James Black Foundation Limited | Benzotriazepnes as gastrin and cholecystokinin receptor ligands |
-
1962
- 1962-09-11 US US222940A patent/US3176008A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094871A (en) * | 1977-02-16 | 1978-06-13 | The Dow Chemical Company | 1,3,4-Benzotriazepine-2-thiones |
| US4144233A (en) * | 1977-02-16 | 1979-03-13 | The Dow Chemical Company | Method for preparing benzo-(1,3,4)-benzotriazepines |
| US4168310A (en) * | 1977-02-16 | 1979-09-18 | The Dow Chemical Company | Psychoactive 1,3,4-benzotriazepine-2-thiones and a method for treating central nervous system depression and anxiety |
| EP0102580A1 (en) * | 1982-08-26 | 1984-03-14 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 1,3,4-benzotriazepines, a method of preparing the same and theire use as medicaments |
| US4482547A (en) * | 1982-08-26 | 1984-11-13 | Hoechst-Roussel Pharmaceuticals Inc. | Substituted-1,3,4-benzotriazepines |
| US20060003993A1 (en) * | 2001-11-13 | 2006-01-05 | James Black Foundation Limited | Benzotriazepnes as gastrin and cholecystokinin receptor ligands |
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